Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation

[Image: see text] Formal hydroperfluoroalkylation of enones is achieved in a two-step process comprising conjugate hydroboration and subsequent radical perfluoroalkylation. The 1,4-hydroboration of the enone is conducted in the absence of any transition metal catalyst with catecholborane in 1,2-dich...

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Autores principales: Jana, Kalipada, Mizota, Isao, Studer, Armido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7901661/
https://www.ncbi.nlm.nih.gov/pubmed/33530687
http://dx.doi.org/10.1021/acs.orglett.0c04260
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author Jana, Kalipada
Mizota, Isao
Studer, Armido
author_facet Jana, Kalipada
Mizota, Isao
Studer, Armido
author_sort Jana, Kalipada
collection PubMed
description [Image: see text] Formal hydroperfluoroalkylation of enones is achieved in a two-step process comprising conjugate hydroboration and subsequent radical perfluoroalkylation. The 1,4-hydroboration of the enone is conducted in the absence of any transition metal catalyst with catecholborane in 1,2-dichloroethane, and the generated boron enolate is in situ α-perfluoroalkylated with a perfluoroalkyl iodide upon blue LED irradiation in the presence of an amine additive. Both reactions proceed under very mild conditions at room temperature.
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spelling pubmed-79016612021-02-24 Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation Jana, Kalipada Mizota, Isao Studer, Armido Org Lett [Image: see text] Formal hydroperfluoroalkylation of enones is achieved in a two-step process comprising conjugate hydroboration and subsequent radical perfluoroalkylation. The 1,4-hydroboration of the enone is conducted in the absence of any transition metal catalyst with catecholborane in 1,2-dichloroethane, and the generated boron enolate is in situ α-perfluoroalkylated with a perfluoroalkyl iodide upon blue LED irradiation in the presence of an amine additive. Both reactions proceed under very mild conditions at room temperature. American Chemical Society 2021-02-02 2021-02-19 /pmc/articles/PMC7901661/ /pubmed/33530687 http://dx.doi.org/10.1021/acs.orglett.0c04260 Text en © 2021 The Authors. Published by American Chemical Society Made available through a Creative Commons CC-BY-NC-ND License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html)
spellingShingle Jana, Kalipada
Mizota, Isao
Studer, Armido
Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation
title Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation
title_full Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation
title_fullStr Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation
title_full_unstemmed Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation
title_short Preparation of α-Perfluoroalkyl Ketones from α,β-Unsaturated Ketones via Formal Hydroperfluoroalkylation
title_sort preparation of α-perfluoroalkyl ketones from α,β-unsaturated ketones via formal hydroperfluoroalkylation
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7901661/
https://www.ncbi.nlm.nih.gov/pubmed/33530687
http://dx.doi.org/10.1021/acs.orglett.0c04260
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AT mizotaisao preparationofaperfluoroalkylketonesfromabunsaturatedketonesviaformalhydroperfluoroalkylation
AT studerarmido preparationofaperfluoroalkylketonesfromabunsaturatedketonesviaformalhydroperfluoroalkylation

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